


The Worst

by orphan_account



Category: Teen Wolf (TV)
Genre: Alternate Universe - Canon Divergence, Begging, Bottom Derek Hale, Butt Plugs, Come Marking, Dildos, Feelings, Fisting, Fluff, Fluff and Smut, Humiliation, M/M, Phone Sex, Plot What Plot/Porn Without Plot, Self-Fisting, Sex Toys, Voyeurism, being a power bottom is also part of werewolf powers, bottom!Derek, dom!stiles, double fisting, feelings and fisting at the same time, romantic double fisting, sub!derek
Language: English
Status: Completed
Published: 2013-08-08
Updated: 2014-02-23
Packaged: 2017-12-22 20:52:45
Rating: Explicit
Warnings: Underage
Chapters: 5
Words: 10,548
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/917897
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Stiles Stilinski was no stranger to weird boners. After all, he was a 16 year old boy who was inexplicably constantly surrounded by perfectly muscled hunks, and that was even before he’d started hanging out with werewolves. From Danny crashing into him at lacrosse practice to treading water while holding up a paralyzed Derek to being paralyzed half on top of a paralyzed Derek to being pushed up against a wall by an angry Derek to...well you get the picture. TONS of experience with weird boners. And pulling an impressive collection of really, really enormous anal toys out of a locked trunk in an upstairs bedroom of the house where Derek Hale’s entire family burned to death? That boner maybe took the cake.<br/>--<br/>Stiles discovers something unexpected about Derek. (formerly titled "What's in the box?")</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Yeesh this is my first fic I hope you like it. Thanks to H and C for their support. <3
> 
> This takes place between the end of season two and the beginning of season three. Stiles is 16. Derek is idk however old Derek is supposed to be.

Feeling smug about his new lock-picking abilities, Stiles opened the lid of the old trunk-- finding himself face to face with a dildo the size of his own head.

What?

WHAT?

He’d been expecting a sweet ancient weapon or maybe some super secret books on werewolf lore, a grimoire or a haunted ventriloquist dummy, even heirloom china from great aunty Hale; something supernatural or dangerous or at least depressing and old. You know, something NORMAL (or at least normal for him.) Stiles Stilinski was not under any circumstances expecting to find the tantalizingly always-locked trunk full of new-looking alarmingly large sex toys.

There was something in there the size and shape of a traffic cone, but black and smooth and completely solid. Oh god. The only explanation Stiles could think of was that Derek had put them there as a deterrent in the highly unlikely (well pretty unlikely, kind of unlikely, okay fine VERY PROBABLE) event that Stiles would break into the trunk looking for magic crap. Stiles smirked, pulling the large toys out and putting them on the floor. He was raised on the Internet. It was gonna take a hell of a lot more than a couple of gargantuan dildos to scare him away from a forbidden trunk definitely full of awesome ancient magic junk.

His hand found itself around a large black plastic bottle. Stiles pulled it out and examined it. The label had a picture of a moon, and appeared to be in German. Bingo. He opened his smartphone’s German translation app (protip: if you’re doing supernatural research, you need a German translation app) and hastily copied the word “Gleitmittel” from the label on the bottle. Okay okay so it’s a neuter noun, synonyms “Gleitcreme” and “Schmiermittel” and the English meaning is...lubricant. A deep blush crept its way across Stiles’ face. He was holding Derek Hale’s half-empty fancy bottle of German moon lube. Part of Stiles was certain that Derek wouldn’t have all this stuff unless it was part of an elaborate ploy to teach Stiles a lesson about snooping, and the other part of him was hoping to prove the first part of him wrong. As he pulled out intimidating butt plug after intimidating butt plug, a box of tattoo artist gloves, a pair of shoulder length disposable gloves with a picture of a horse on the packaging, and a container of Crisco, Stiles realized it would have had to be a really, REALLY elaborate scheme.

Stiles Stilinski was no stranger to weird boners. After all, he was a 16 year old boy who was inexplicably constantly surrounded by perfectly muscled hunks, and that was even before he’d started hanging out with werewolves. From Danny crashing into him at lacrosse practice to treading water while holding up a paralyzed Derek to being paralyzed half on top of a paralyzed Derek to being pushed up against a wall by an angry Derek to...well you get the picture. TONS of experience with weird boners. And pulling an impressive collection of really, really enormous anal toys out of a locked trunk in an upstairs bedroom of the house where Derek Hale’s entire family burned to death? That boner maybe took the cake.

Stiles’ brain was going a mile a minute. Weirdly enough, Stiles had never given Derek’s sexuality much thought. Stiles knew he’d been involved with Kate Argent at one point, but for obvious terrifying psycho bitch reasons, he didn’t think about what that relationship had been like. Stiles always figured that since Derek wasn’t into having fun, and since sex was (probably, from everything Stiles had heard) fun, then, by the transitive property, Derek wouldn’t be into sex. He pictured Derek as the type of guy who would rather self-flagellate then squeeze one out, or at least try to work off a boner with like a thousand push-ups.

But hey, what did Stiles know? Here was pretty convincing evidence that Derek was way more interested in sex than he’d ever let on. As much as Stiles tried to convince himself that it made some sense for big bad sourwolf alpha Derek to be into putting enormous things in people’s butts, he just couldn’t picture Derek going to a sex store. Not that the guy wasn’t hot, and not that Stiles had never thought about it, because duh muscles cheekbones stubble penetrating stare permanent frown sexy eyebrows and um constantly shirtless and often wet and growling much? But Derek didn’t exactly exude an aura of trustworthiness, at least not until you got to know him. Maybe they weren’t his after all. Maybe they were Peter’s (maybe) or...Isaac’s (no)...or Erica’s? Was Stiles handling a dead person’s sex toys?!

“Stiles.”

And of course, because this wasn’t already weird enough, the one person Stiles least wanted to catch him holding a 2 foot long set of anal beads (except maybe his dad or ugh Finstock that would be pretty bad or one of the Alphas because duh violence) was standing in the doorway all perfect and muscled and cocking a beautiful eyebrow and frowning.

“Heyyy Derek,” Stiles tried to keep his heartbeat calm, knew that Derek could tell if he was hiding something, smell his anxiety and --fuck probably also smell his weird arousal. Stiles tried to stare at the ground but woops the ground was covered in giant sex toys and Derek was walking into the room and by the time Stiles looked back up at Derek, expecting either rage or delight at his embarrassment, Derek’s face was turning a distinct shade of humiliated red.

Well that answered the question of whose trunk it was. As irresistible as teasing Derek usually was, Stiles quickly found himself trying to explain himself and make Derek feel better and make this whole weird situation go away and also maybe make his boner not be a boner anymore because at this point it was just rude.

“ListenI’djustnoticedthetrunkinherebeforeandIalwayswantedtolookinsideandIgotthislockpickingkitfromthespystoreandIfiguredyouprobablyhadcoolmagicshitinsideIdidn’tknowIswearandI’mnotjudginglikeit’sfinetobeintowhateveryou’reintoI’mnotkinkshamingandIpromiseIwon’ttellanyonedudelet’sjustforgetit.”

“What?”

Deep breaths. Okay.

“Ummm dude it’s fine I don’t care if you like to put giant things in people’s butts you know that’s cool I’ve seen way weirder in porn online I won’t tell anyone just like you know be safe! Lube up! Not that I’d know because hey big virgin over here but I’m happy for you dude that you’re doing whatever it is you’re doing here. And I’m sorry for snooping I will never break into your stuff again.” Stiles looked up hopefully. He’d never seen Derek look so vulnerable, not even when he was paralyzed or almost dying and clearly Stiles’ dick was defective or sociopathic or something because watching Derek going full-body blush was somehow making him even harder.

Derek spoke softly, eyes glued firmly to the floor in front of him. “I don’t ‘put giant things in people’s butts,’ Stiles.”

“Whatever man, like I said, whatever it is you’re doing. It’s cool!” Stiles needed to get out of there. His jeans were too tight against his straining cock. The air was too thick with dust and mildew and the smell of latex. “I should probably just--”

“I put them inside of myself,” Derek said in something between a whine and a whisper. Stiles choked as the image of macho alpha hunk Derek Hale splitting himself open on a shiny black dildo, blushing and desperate and slutty, flashed through his mind. All he could do was bolt, trying not to jizz in his jeans (Derek would DEFINITELY be able to smell that), running back to the Jeep, fumbling with his belt buckle, and coming messily onto his fingertips a nanosecond after taking out his cock. His phone buzzed. A text from Derek: “Tell. No one.”


	2. Chapter 2

**Notes for the Chapter:**

> oh my gosh I am a MONSTER for waiting so long to update this!!! I started working on other fics and kind of forgot about this one. because I am a monster. feel free to hate me. I'm going to try to do another update again soon. sorryyyyyy
> 
> thank you to [homosadpornien](http://archiveofourown.org/users/homosadpornien) for being like the most encouraging friend ever <3

Stiles told no one, not out of fear, or even out of compassion, but because he liked having a secret that for once didn’t have to do with someone getting maimed or killed. Once he’d gotten over the initial shock, Stiles moved onto what he did best: obsessive research and frequent masturbation. Anal training was something that took time and discipline to accomplish (two things that Derek had plenty of), but the lack of beginner, intermediate or even normal advanced level toys in the trunk led Stiles to hypothesize that Derek’s werewolf healing and stamina gave him an extra edge that allowed him to skip right to pretty extreme play.

Unfortunately, there was a real lack of materials on werewolf sexuality, at least that were available to Stiles. He used to go to Scott with these sorts of questions, but now any mention of sex or romance sends Stiles’ best friend into a misty-eyed Allison-nostalgia melancholy. Deaton was the next logical person to ask. Dude was like a walking supernatural encyclopedia, and visiting his office meant Stiles got to play with puppies. It’s not like Stiles had never asked Deaton a fucked up werewolf sex question before, but in the past he’d always just blurted them out when they popped into his head. He’d never gone to the clinic deliberately just to ask about knotting or mating or heat cycles or foreskin regrowth. Maybe if it came up naturally? “Hey doc shame about that alpha pack oh that reminds me are werewolves capable of amazing feats of anal gymnastics?” Nope. Not even Stiles could pull that one off.

Obviously, Stiles wasn’t going to approach Derek about it. Since the uh...incident with the trunk, things had gotten really weird between them. Stiles had tried to be extra nice, but Derek had shifted from grumpy to just plain mean. Definitely not receptive to questions about his anal stretching techniques. Would it be rude to accuse him of using werewolf skills to cheat? Like accusing an athlete of taking steroids? Didn’t matter because Stiles wasn’t going to ask him. That left Isaac and Peter. Assuming Isaac had experimented before and after receiving the bite, he’d be able to provide data on any change the bite may have had. Peter, on the other hand, would have much more general knowledge about werewolf anatomy. This was the point where Stiles usually gave up on research and shifted gears to furious masturbation.

Naturally he’d started watching kind of a lot of extreme anal porn (FOR RESEARCH!!!) and hey whaddaya know, it didn’t take too long (only a cumulative 30 hours of intense xtube searching, but who’s counting?) to find a video featuring a guy with Derek’s build spearing himself on one of the very toys Stiles had found in The Trunk. So obviously he had watched it a bajillion times and bookmarked it and pretended it was a video of Derek. Because research. And yeah, maybe he’d let it heavily influence his masturbatory fantasies about Derek.

Jerking off while thinking about Derek was nothing new. Even back when Stiles thought the guy was just a creepy murderer, those steely creeper eyes and that ridiculous bone structure and the fucking MUSCLES popped into his head pretty regularly. By the time Derek had become big bad alpha, he was pretty much the star of most of Stiles’ masturbatory fantasies. Thing was that back then, Stiles thought big bad alpha meant big bad top, that Derek would be smirkingly confident and in charge, pushing him up against walls (which to be fair, happened outside of his fantasies too), manipulating his scrawny limbs, teasingly opening him up with thick, wet fingers before sliding in and fucking him until he fell apart. But hot as that fantasy was, Stiles found himself drifting away from it more and more since he’d opened The Trunk.

Now more often than not when Stiles jerked off thinking about Mr. Big Bad Wolf, _Derek_ was the one gagging on _Stiles’_ cock, drooling and begging for it, pathetic and needy and wrecked. It only complicated things that Derek was quickly filling Jackson’s shoes as the biggest douchebag in Beacon Hills. Seriously. Sometimes _Peter’s_ eyes would widen in shock at the shit Derek said to Stiles. Stiles could handle dismissive. He could handle dramatic eyerolls at his hyperactive antics. But when Derek started making snide, intentionally hurtful remarks about Stiles’ sexual inexperience and physical weakness? About his dad being a bad sheriff? About the level of Stiles’ bravery and dedication to the pack? During pack meetings? What the fuck? And Stiles _knew_ it was just because he’d found out Derek’s dumb secret that wasn’t even that big of a deal anyways.

So Stiles fantasized about doing and saying things to him he’d never thought he was interested in before, maliciously taunting Derek, demeaning him, laughing at him. Things like fucking Derek with an aluminum baseball bat or a huge silicone werewolf dildo (complete with knot), Derek begging to be bred like a bitch. Things that when Stiles was catching his breath, come cooling on his belly, made him think “where the fuck did THAT come from?” Things he felt guilty about until he finally retorted to the alpha’s latest insult with “go choke on a dick Sourwolf” and Derek fucking blushed. And it turned out the more Stiles challenged Derek, the nicer Derek got. So Stiles’ guilt subsided, because Derek fucking _liked it_.

It didn’t take long after that for Stiles to test how much further he could push it.


	3. Chapter 3

**Notes for the Chapter:**

> yesssss finally!! thank you to H & C for getting so excited and being so awesome and supportive of me writing this.

**sup dude**

Stiles figured starting a text conversation normally couldn’t hurt, sprawled out on his bed fresh from the shower, towel still tied loosely around his waist.

**What do you want Stiles?**

He rolled his eyes. Predictable response.

**i have questions**

No reply. Maybe this wasn’t going to work.

**And???**

What a dickweed. Okay. Here goes nothing.

**does your werewolfitude help when you fuck yourself on huge stuff**

**is it like super healing and strength and stuff?**

**or do you have to stretch yourself like everyone else**

Stiles took a deep breath. In through his nose and out through his mouth. This was exciting! Nerve-wracking yes, possibly dangerous, but exciting and kind of hot.

**I’m not talking to you about this.**

Stiles smirked. Like hell he wasn’t. He opened Derek’s contact info and pressed “Call.”

_“I’m not talking to you about this Stiles.”_

“You know you want to. All it takes to get you blushing is the slightest allusion to a dick being inside you. Come on Derek.”

Stiles could bet Derek was blushing right then. He could hear Derek sputtering through the phone.

“It’s cute though. I like it.” Stiles hadn’t realized that before, but yeah, it _was_ cute when Derek blushed. The tips of his ears would get red too and he would just kind of stare at the floor. It was adorable.

 _“Why?”_ Derek’s voice was low and dark, full of suspicion. _“Why do you want to know?”_

“Dude I haven’t been able to stop thinking about it.”

Silence.

“I haven’t been able to stop thinking about _you_ ,” Stiles corrected, which was true, but left him feeling oddly vulnerable. Derek exhaled though in a way that signalled some kind of acceptance. “Just tell me big guy. It’s me. It’s _Stiles_. I’m always asking about weird crap.”

 _“Um,”_ Derek cleared his throat and spoke tentatively. _“I don’t know if it’s a werewolf thing or not. I’ve never not been a werewolf. I have to work to open myself up like anyone else, I guess. It helps to wear a plug under my clothes.”_

It took Stiles a couple of seconds to remember to breathe. “Yeah?” Derek wouldn’t notice if he jerked off to this, right? He was already basically naked. Stiles let the towel fall off and wrapped a hand around his hardening cock.

_“Um...yeah.”_

“Like when?”

 _“Stiles…”_ Derek tried and failed to sound threatening. It came out as more of a whine.

“Do you just walk around with a plug secretly in your ass? Like to the store or the gas station or oh shit do you wear one during PACK MEETINGS?”

Derek’s annoyed exhale was all the answer Stiles needed.

“Oh my God you DO don’t you? Walking around in your fucking badass leather jacket shooting people scary alpha stares and growling but LITTLE DO THEY KNOW that under those jeans you’re stretching yourself open so you can go home and impale yourself on something huge?”

Derek exhaled loudly again, but this time he didn’t sound annoyed. He sounded more like...holy shit. Was that a _pant_? Stiles shut himself up for a couple of seconds, and sure enough, Derek’s breathing had sped up and intensified.

“Derek?”

 _“WHAT?”_ (Okay, there was that annoyance again, but still too breathy to be normal.)

Stiles smirked. “Whatcha doing Derek?” He put a condescending lilt into his voice that never failed to piss people off.

_“Fuck off Stiles.”_

“Oh, okay. Do you want me to leave you alone? I can hang up. See, it SOUNDED to me like you were jerking off while I was talking, but I can go. I’ve got plenty of things to do. Me? Stiles? A guy with stuff to do. So you have yourself a--”

Derek’s growl assaulted Stiles through the speaker. _“Shut up and keep talking you little shit.”_

Stiles couldn’t help the grin that spread across his face. “Derek buddy, you aren’t making sense. How am I supposed to shut up and keep talking?”

Derek replied with a frustrated grunt. This was fucking awesome. Stiles never knew that trolling someone could be so hot.

“Fine. What do you want me to talk about? I can tell you about my day-- thanks for asking _by the way_ \-- it was fine. Orrrr I can talk to you about Scott? He’s on a whole self-improvement kick--”

_“STILES”_

“What?” he asked, widening his eyes as if Derek could see him, imbuing his voice with fake innocence. “Ohhh! Did you want me to talk more about YOU? About how you’re the alphiest alpha-- alpha-y-est? alpha-est? whatever-- How you’re a big bad wolf who makes everyone tremble and quake in fear? Hmm...what was I saying before? You’re a big tough alpha wolf with a badboy leather jacket...pushing poor defenseless teenage boys up against lockers...intimidating everyone...ohh right! And all this time you’ve been secretly plugged up and stretched open, ready to be fucked.

“Do you wear it every day Derek? I didn’t see any normal sized butt plugs in the trunk. Were you wearing it when you found me there?”

Derek’s panting had resumed, occasionally punctuated by choked back moans. Stiles was hard, but was in no real hurry to jerk off and come. The familiar adrenaline rush he always got when he let his smartass mouth run amok was there, and so was the mischievous curiosity, that nagging question of “How far can I go?” But they were joined by new feelings of heady satisfaction and control.

“Hellooo? Derek? This isn’t fun unless you answer me. I’m just going to hang up.”

 _“Yes,”_ Derek gritted out.

“Yes what? Yes to which question? You’re a big boy. You can use your words.”

_“Yes I wear it every day. Yes I was wearing it when I found you.”_

“That’s so fucking hot,” Stiles blurted out, blushing suddenly. Seriously? He was talking Derek off no problem but admitting that he thought it was hot made him blush?

 _“...Really?”_   If Stiles didn’t know better, he’d think Derek sounded insecure. Is that what was going on?

“Um yeah ‘really’ dude.”

Derek let out a loud whiny _“Nngh!”_ which Stiles guessed meant that he was happy with Stiles’ admission.

“Why do you think I brought it up? I’ve been whacking off thinking about this for weeks.”

Derek choked off another groan.

“Stop doing that dude. I want to hear the sounds you make.”

Another heavy breath. _“Okay.”_

“Do you have it in now? You do right?”

A long groan. _“A different one. Bigger.”_

Stiles understood on some intellectual level that he was supposed to be making this hot and talking dirty, but he either couldn’t or just didn’t want to stop himself from asking questions. “So do you touch your dick when you do this or do you come untouched? Can you knot even when your dick isn’t inside of something else? Do you put the toy on the ground and then lower yourself onto it or bend over and reach behind you or what?”

 _“Stiles.”_ Ha. Derek could sound exasperated even when he was masturbating.

“Sorry sorry. But for real Derek, two questions. One: are you touching your cock? And Two: are you now or have you ever knotted the air?”

_“One yes-- nnnggh-- two no.”_

“Why did you tell me the truth that day? Why didn’t you lie?”

_“Wanted you to know. Like that you know.”_

Interesting. And hot. Hot and interesting. “Did you fantasize about being found out before? What did you think I would do? Tell everyone and humiliate you? Did you think we’d do something about it? Treat you like a whore, passing you around, taking turns filling you up?” Okay, Stiles could talk dirty if necessary (a silent prayer of thanks to the Internet.) Derek’s humiliation thing was hitting his buttons in a big way.

Derek fucking GROWLED at that. But his voice was softer when he replied, _“just you.”_

Stiles was taken aback by the admission. He’d figured this was just a standard exhibitionist thing, not something so personal. Really? HIM? Stiles wasn’t sure how he felt about that. “Why me?”

 _“Stiles--”_ it came out like a whine, a plea.

“Why me Derek?”

Derek fucking whimpered in response. It was the closest he’d ever come to sounding like an actual canine. He was panting now, breathing hard and heavy and fast, like he was about to--

“Derek I swear to god if you fucking come before you answer me I will never talk to you again. Take your hand off your cock right fucking now and don’t even think about moving until I say you can.” Stiles’ skin was buzzing, not in the too tight anxious Adderall way, but in the veins pumping pure electricity, whole body thrumming brilliantly way. It was invigorating.

Derek roared in frustration, but his breathing slowed. _“It’s hard to explain.”_

Well thanks a lot dickbag. This was the closest he’d gotten to someone admitting to being into him since Erica had confessed her childhood crush, and Derek didn’t even know why?

Stiles could hear Derek taking a deep breath before speaking. _“You’re so quick. You’re smart. You think fast and talk fast. You make my head spin when I try to keep up. It makes me feel...not weak or small, but something close to that.”_

“Are you saying that I humble you?”

_“Yeah. You’re not afraid to give me shit.”_

Stiles smiled, feeling flattered and kind of touched. “You like that I’m not impressed by you, huh? That I put you in your place?”

Derek moaned. (To be fair, Stiles had put the heat back into his voice.)

He couldn’t help but chuckle at that. “So do you like, fantasize about me? Oh! You can touch your dick again if you want.” Stiles asked, wrapping his fingers back around his neglected cock and resuming a gentle rhythm.

 _“Stiles,”_ Derek whined, which was a yes in Stiles’ book.

“Whining my name is a ‘yes’ in my book.” Stiles was feeling more than a little bit giddy, combined weirdly with the heat pooling in his belly as his strokes grew firmer. It was a lot, and yet Stiles’ focus was still needle sharp, every cell in his body singing **derekderekderekderek**. “Tell me,” he urged, breath hitching slightly.

 _“Your hands. Your fingers.”_ Derek’s voice was all gravel and heat.

“Opening you up? No...I bet you want me to do it afterwards when you’re all fucked out.”

Derek’s breathing was getting faster again. Huffing and puffing desperately. Fuck that was hot.

“Fuck you to pieces on one of your crazy-ass toys and then pull it out? Feel your used-up fucked-out slutty hole?”

 _“Unhh!”_ Derek sounded wrecked, fucking _destroyed_ , which would have been hot enough, but the knowledge that it was STILES doing this to him was too fucking much.

“Yeah Derek?” Oh God Stiles was getting close. (He’d need to give himself a pat on the back later for holding out this long in the first place.) His breath was coming fast, his muscles tensing. “That’s what you think about? Showing a fucking sixteen year old boy how _messy_ and _loose_ you are? Fuck that’s so fucking _dirty_ Derek.” He was just babbling at this point, his approaching orgasm making his lack of brain to mouth filter more apparent than ever as his thoughts grew frantic.

 _“Stiles, fuck I’m--”_ And Derek let out a sound that was half groan half roar, more animal than human.

Stiles could hear his own panting, so high pitched and human in comparison. A string of curses poured out of his mouth. So close. So fucking close.

It was hearing Derek’s voice, blissed out and warm, soft around the edges, still a little breathless, saying _“Thank you Stiles”_ that pushed him tumbling over the edge.

Stiles laid back and caught his breath, wiping away the puddle of come on his belly with a towel, too lazy and sleepy to grab a tissue. He was just settling in to enjoy the afterglow when he heard the familiar sound of his dad’s police cruiser pull into the driveway. He hissed out a quick “Shit! My dad’s home. I’ll talk to you soon,” before hanging up and turning off his bedroom light.

Had that been rude? What had just happened? Did this change things between him and Derek? Well obviously. But how so? Ugh. Fuck. Stiles’ phone buzzed, interrupting his mounting panic.

Derek had sent him a picture. Of...his face? Derek with his eyes heavily lidded and pupils blown out, lips parted slightly, fingers in his mouth, eating something thick and pearlescent. “That would be semen, Stiles,” he muttered to himself. Derek eating his own come. Well that was disarmingly hot. A second message came through:

**Thanks.**

With a smiley face emoji. Any feeling of control or mastery over the situation at hand was long gone with the knowledge that Derek used emoji.

Not sure what else to do, Stiles texted back:

**you too. night derek.**

He threw in a wolf, a moon, and a cool sunglasses guy for good measure, before plugging his phone in and letting himself fall into a very well-deserved slumber.


	4. Chapter 4

**Summary for the Chapter:**

> Stiles and Derek find themselves back at the old Hale house, but this time they're looking in the trunk of sex toys together.

**Notes for the Chapter:**

> Oh my goshhhh thank everyone for the really lovely comments!! Big huge extra special thanks to [neerdowellwolf](http://archiveofourown.org/users/neerdowellwolf) for letting me bounce ideas off of her and putting up with my constant hand wringing about what I wanted to do with this chapter. YOU ARE THE BEST!!! <3

It was one of those stupidly hot late August days that made Stiles really rethink his decision to grow out his buzzcut-- he could feel the sweat soaking through his t shirt and dripping down his face. If he was a reasonable person, he would have figured out a way to get Lydia to let him use her pool, or at least be spending the day hanging out naked in his bedroom with the A/C on full blast. But no. Instead, Stiles was walking into the burnt out shell of Derek Hale’s ancestral home in order to watch a ripped alpha werewolf put something really, really big in his own ass.

Derek was already inside, buff and shirtless and somehow still looking hot in the stifling heat, the light sheen of sweat on his skin looking like something out of an underwear ad. Typical.

“Sooo how do we do this? I know this may come as a surprise, but this is actually the first time I’ve met a guy in an abandoned house to watch him do crazy anal stuff.”

Derek blushed a little and glared. “It’s not like a make a regular habit out of this _Stiles._ ”

“Well umm are you prepped?” Derek looked at the floor and nodded shyly. “Do you have a toy picked out?” Derek shook his head. “Should I pick one out?”

Derek’s “okay” was quiet. He shifted his weight back and forth. Who was this guy and what had he done with Derek Hale? “Dude, if you’re having second thoughts or don’t feel up to it or whatever, it’s totally not a big deal.” Stiles patted Derek’s forearm in what he hoped was a reassuring way, but Derek looked up at him, eyebrows furrowed.

“Do you not want to?”

“What? Who? Me? Stiles? Stiles wants-- I mean, I want to. Do this, I mean. I want to do this. You could put “wants to do this” in quotation marks between my first and last name. I am like the president and founder of the wanting to do this council. I--”

“Okay, I get it.” Derek was trying to sound annoyed, but he was smirking just a little bit. (Stiles Stilinski: making people feel better by acting like a complete jackass since 1997.)

Stiles reached into the trunk and pulled out one of the black silicone traffic cone looking things. It was a little over a foot long and had a ribbing design going across it instead of being perfectly smooth. The tip was shaped like a cross between a pyramid and a cockhead. “What about [this one](http://thepleasurechest.com/images_products/11629_big.jpg)?” Thinking about Derek fucking himself on it was already making Stiles kind of hard. The alpha just nodded and undressed quickly, pulling a bottle of that German moon lube out of the trunk before closing the lid, gesturing for Stiles to sit down. He took the toy from Stiles’ hands and set it on the ground. The base turned out to be some kind of suction cup, and Derek tested the seal a couple of times before generously drizzling some lube over the toy, squatting over it, and slowly sinking down so the tip was inside. He leaned back, hands behind him supporting his weight, legs spread open and feet flat on the floor, bracing him and giving him leverage. He continued to sink down, at an angle now, giving Stiles a perfect view of the toy, slick and shiny with lube, breaching Derek’s asshole.

Derek got about half of the length in and started to ride it slowly, each time sinking down just a tiny bit further. Neither of them spoke, the only sounds the occasional breeze rustling branches or an animal walking past outside, the wet _shlrk_ of Derek fucking himself over soft grunts, Stiles’ blood pounding in his ears, both of their breaths growing ragged. By the time Derek was three quarters of the way down, beads of sweat were dripping down his forehead and his calves, his groans getting louder. Stiles wouldn’t have been surprised to find himself drooling. No amount of fantasizing and nothing on the internet, no matter how intense or extreme, could have prepared him for the sight of Derek’s pink hairless hole stretching progressively wider and wider around the toy, his fat uncut cock half-hard and bouncing, the muscles in his legs working and flexing. His eyes were closed and his lips were parted, face flushed from more than just the heat. Fuck he looked good.

Apparently Stiles had said that last part out loud, because Derek was opening his eyes and looking at him with this expression that was absolutely _wrecked_ with need. Stiles’ body was buzzing under Derek’s gaze, dick hard in his jeans. “How does it feel?”

“Hng...feels...big. Full.”

“Good?”

“Yeah,” Derek said in a low whine.

Stiles felt hints of that sharp focus he would get when he did this with Derek (whatever “this” was), but the heat was too oppressive, making him a little bit too sluggish to get there. “Can you get it all the way in?”

Derek nodded and closed his eyes again, lifting up almost all the way off of the toy, taking a deep breath and then bottoming out in one fluid motion. His jaw clenched and he breathed hard through his nose, getting his body used to the invasion. Stiles found himself walking over, crouching in front of Derek to get a better look. Derek’s cock had leaked a little bit of precome, Stiles noticed idly, letting his eyes wander down to where Derek was stretched at least four inches wide around the toy. He knew for a fact that Derek could take more, but the rim was flushed with arousal stretched so fucking taut, it didn’t look like it could stretch any wider. “Can I just--”

“Please,” Derek moaned.

So Stiles tentatively touched Derek’s rim with his fingertip. It was even hotter than the air around them, slippery with lube and it felt delicate-- which is a word Stiles never thought he’d use about Derek Hale. “Fuck,” Stiles whispered, eyes wide, softly tracing the stretched circumference. Derek shuddered periodically, his head falling back as he groaned. They found some kind of rhythm together, Derek grinding against the toy and Stiles gently moving his finger clockwise and counterclockwise. But then Stiles’ fingertip traveled up instead of around, up the smoothness of Derek’s taint, over his balls and it only felt natural to brush his fingertips up and down Derek’s cock before gripping it loosely. And then Derek was sitting up and Stiles’ other hand was on his shoulder and their faces were awfully close together and Derek was bouncing up and down on the toy again, Stiles moving with him, jerking him off in time. And this was hot. This was really really fucking hot. Derek looking right into his eyes, pupils blown, huffing and puffing as he fucked himself, breath hot in Stiles’ face.

Stiles took his hand off and spat in it before resuming his ministrations, jerking Derek off with a mixture of spit and precome and lube and both of their sweat, which should have been gross, but it just ended up being hot. Derek seemed to think so too, because he groaned out a “ _Fuck_ Stiles” when Stiles spat in his hand. Stiles looked at him inquisitively and Derek’s blush spread to his ears, spearing the toy back into himself. “Hng...your spit...’ll make me smell like you.”

Stiles smirked, pulling just a little bit harder on Derek’s dick. “You want to smell like me? Is that a werewolf thing? Like marking territory?” He clearly said the right thing because Derek stilled,  eyes saucer wide, looking like a cross between a kid seeing Disneyland for the first time and a deer caught in the headlights (albeit a _really horny_ deer.) “Do you want me to mark you Derek?” His nostrils flared and he nodded. “Okay, what do you need me to--”

“Come on me.” It wasn’t a command as much as it was just a statement. His eyebrows furrowed. “Please.”

An alarm went off in the back of Stiles’ mind. He was about to have sex. Non-penetrative sex sure, but still. Sex! He did the best he could to hide the giddiness that welled up inside him because this was not what he was expecting at all and was, to be perfectly honest, pretty fucking awesome. “Okay,” he said, standing up, “I think I can manage that.” He removed his sticky shirt and toed out of his shoes. Even the stale air of the house was a huge relief on his overheated skin, so he took his pants and boxers off, too hot to feel bashful about his comparatively scrawny pale frame.

Stiles knelt back down in front of Derek, not really caring that he was getting his knees dirty with dirt and dust and ash, squirting some lube into his hand and starting to stroke his dick. Derek took that as a cue to start fucking himself again, leaning back and taking it at an angle so each ridge would rub up against his prostate as he moved. Under normal circumstances, Stiles probably wouldn’t have been able to last longer than a couple of minutes, but the heat had his body so relaxed that he was able to jerk himself off leisurely, taking in the view of Derek taking so easily what he had been a struggle to fit inside himself before. “You should see yourself, stretched open and loose, dripping lube, taking it so well. God _damn_ Derek…” Derek preened at Stiles’ praise, picking up his pace, moving harder and deeper with renewed determination. Stiles followed, jerking himself faster, feeling his balls tightening. “So much hotter like this. No pushing anybody around, no alpha swagger, just you on the floor splitting yourself apart…”

Stiles continued to babble nonsense as he felt his orgasm build, it couldn’t have been anything too bad though, because Derek was moaning and whining, panting out the occasional “Stiles!” and fucking himself frantically on the toy. And then Stiles was coming, whining out a long “fuuuuuuck” and shooting hot and sticky and thick over Derek’s abs and chest, hitting him a couple of times in the face. After the last wave hit, Stiles found himself exhausted and overheated and out of breath. It took him a few seconds to realize that Derek was rubbing Stiles’ come into his skin and murmuring “thank you” over and over again. Quickly filing that image away into his mental spank bank, he reached for Derek’s cock with his already lubed up hand. “Come on Derek.” And it didn’t take long for Derek, grinding his hips and murmuring softly under his breath, to do just that, eyes flashing red as his climax hit.

* * *

That night, long after Stiles had washed all the dirt and sweat and come away, cool and comfortable in his air conditioned room, he still felt some of that residual heat burning under his skin, like a sunburn only sexier. He fell asleep smiling.

**Notes for the Chapter:**

> so the toy in the story is a fictional toy based on the Titanmen Intimidator, which is made of rubber, not silicone and is slightly smaller than the one Derek uses. also it doesn't have a suction cup.
> 
> Only one chapter left!! Aaaaah excitingggg


	5. Chapter 5

**Summary for the Chapter:**

> fisting and feelings

**Notes for the Chapter:**

> well. here it is. I've been fussing over this chapter for over a month. I started this story six freaking months ago. and now it's finished! hope you like it! (gushing sappy thank you's are in the end notes.)
> 
> [also: this is where the story gets canon-divergencey. basically the deaths at the beginning of season 3 don't happen. (because I didn't want to deal with them.) so, if you're wondering about why Stiles isn't more concerned about the things he's concerned about at the beginning of season 3, that's why.]

“Have you ever fisted yourself?”

It would have been cooler if Derek had done a spittake, but instead he just growled softly, “STILES!”

“What? no one is around and it’s an honest question.” At least Stiles didn’t _think_ anyone was around. He’d shown up at the loft almost an hour early specifically so he could ask Derek fun probing questions. “You’re kinda adorable when you squirm, you know that?” He poked Derek in the side with his finger, because Stiles was a little shit, and no matter what Derek _said_ , he fucking _loved it_. He followed Derek around from room to room. “Well?”

“What?”

“Have you ever fisted yourself? It’s a simple question.”

Derek groaned, exasperated, and sure enough when Stiles checked, there was the outline of Derek’s hard-on, clear as day through the alpha’s stupidly tight jeans. No matter how many times he’d gotten that response out of Derek just on the merit of being obnoxious, it never failed to make Stiles feel giddy.

“I don’t know why you’re asking me this. You know the answer.”

“I do? News to me...”

“The long latex gloves in the trunk? The _fisting gloves_?”

“The horse gloves? I thought those were like a condom lifehack for huge dildos, dude. Not everyone is a freaky anal slut expert.”

Derek blushed, because Derek was predictable. And adorable. To be completely honest, Stiles had been finding Derek to be increasingly adorable and decreasingly annoying lately. He was growing to _really like_ Derek. Which made him kind of nervous if he thought about it too hard, because aside from the fact that Derek clearly fetishized mouthy obnoxiousness, Stiles wasn’t really sure how much Derek liked him at all. So mostly he tried, with varying degrees of success, not to think about it.

The important thing was that Derek _definitely_ fisted himself. Even more important: from the look in his eyes when Stiles taunted him with latex horse gloves in Deaton’s office, wiggling his long fingers before making his hand into a fist, Derek was definitely interested in being fisted _by Stiles_. However, with school back in session, things with the alpha pack heating up in earnest and the discovery of Derek’s long-lost sister, they didn’t exactly have tons of time (or any time at all) to sneak out to the Hale house for sexytimes. Their contact was pretty much limited to pack stuff and texting (sexting), which was fine and cool and not a big deal. It’s not like they were dating or anything. Hell, they’d never even kissed. So Stiles was surprised to find Derek waiting for him in his bedroom when he got back from cross country.

“Hey creeperwolf, it’s been a while since you’ve shown up like this.” Stiles dropped his bag and flicked the light on, remembering that his dad was going to be working all night. And holy fuck. Derek wasn’t leaning nonchalantly over Stiles’ desk, he was _bent over it_. With his _pants down_ , something metal between his cheeks catching the light.

“What the FUCK Derek!? What if my dad had come in here and found you like this?” Stiles was communicating his outrage pretty decently with his mouth, but his body (traitor!) was a dead giveaway. He was trying to stand intimidatingly, maybe shake his fist in a “you dang kids!” kind of way, but instead he was closing the door behind him and getting close to Derek to get a better look. The metal was the slim stainless steel handle of a plug. Derek’s [“every day” plug](http://thepleasurechest.com/images_products/7431_big.jpg), Stiles knew from their text conversations.

Derek rolled his eyes and started to say something (probably something rude and sarcastic, knowing Derek), but before he could talk, Stiles was brushing his hands down Derek’s flank, crouching down behind him, spreading him with long thumbs. Derek sighed under Stiles’ touch, making Stiles smile. The steel of the plug was hot. Stiles hooked two fingers through and pulled, not hard enough to remove it, but hard enough to force an obscene groan out of Derek. He let go and waited a few seconds before doing it again.

Stiles suppressed a laugh. “Do you know why I always fuck with you, dude?”

“Hnng...because you’re a little shit who’s just asking to get his ass beat?” Derek’s head was turned to face Stiles, eyes glowing alpha red.

Stiles stroked his chin, pretending to be thoughtful. “Hmmm, well, I am a little shit. That’s true. But Derek buddy…” He smirked, twisting the plug, making Derek growl. “You’re the only one here begging for something to happen to his ass.” Stiles punctuated his statement by pulling the plug, and then pushing it back in, knowing that the bulbous edge would perfectly hit Derek’s prostate. Derek roared, something that would have made any beta or omega cower in submission, but not little breakable human Stiles, who had no biological predisposition to respect the alpha’s authority. Derek’s claws were out, digging deep into some paperback copy of Dickens, his fangs were dropping. “I fuck with you because,” Stiles pulled the plug out completely, “you just make it too easy.” The metal plug was hot, so hot it almost hurt to touch.

“STILES,” Derek groaned.

Stiles realized that he had been absentmindedly petting the outside of Derek’s loosened hole with his fingertips. He was able to dip two fingers in without any resistance, marveling at how soft and hot Derek was inside. Derek’s ass was still pretty slippery from the lube he’d used with the plug, so Stiles circled Derek’s rim, tugging lightly at it as he went. He probed deeper, listening to Derek’s fast breaths, pressing down lightly when his fingers brushed against the walnut shaped gland. He pulled his fingers out and wiped the lube off on Derek’s thigh. Stiles had an idea.

“Hey Derek,” Stiles said in a stilted voice, a grin spreading across his face.

Derek grumbled at the loss of stimulation. “This can’t be good.”

“Derek, remember what we were talking about before?”

“For fucks sake Stiles...”

“Derek, I just think it would be um...prudent for you to fist yourself. Right now. And I’ll watch.”

Derek turned to face Stiles, cocking an eyebrow. “You think it would be ‘prudent’?”

“You know, prudent, hot. Whatever.”

Derek gave Stiles his best grumpycat face, but it was clear that Stiles had won. “I’m going to need more lube.”

Stiles scrambled to his nightstand, pulling out a white jar that said “SHAFT” on it in big red letters. He handed it to Derek and pulled his desk chair out, taking a seat and watching attentively. Derek dipped his fingers into the jar, taking out a glob of thick creamy goo and reaching back to deposit it inside his hole. Derek took three fingers easily. He fucked them in and out of his ass, spreading the lube around before adding his pinky. The toy Stiles had watched Derek fuck himself with was bigger than all four of Derek’s fingers, but there was something unbelievably hot about watching Derek digging into himself like this. Derek pulled out and got another big glob of lube onto his thumb, which he tucked in against his palm.

Derek groaned loudly, eyes closed, head thrown back, as little by little, he slid his hand into his ass. It didn’t look like he was penetrating himself as much as it looked like he was swallowing his own hand. With his ass. Stiles had FELT that hand, been pushed up against things and manhandled by that hand, punched (lightly, but enough to get the point) by that hand. That was a powerful fucking hand, and Derek’s ass sucked it down like it was no big deal. His hole stretched around his wrist, the hair on his forearm greasy with lube-- the image was fucking gorgeous. He was sweating, taking deep breaths, using his free hand to get more lube and rub it over his forearm. It was a lot like the way he fucked the toy, in that he fucked the object in question into his ass gradually, until he couldn’t stretch backwards anymore.

Stiles wrapped his hand around Derek’s elbow and nudged it upwards. Together they rocked Derek’s arm into him at a slow steady rhythm, Stiles petting Derek’s forearm, stroking his stretched rim, listening to him pant. “Fuck, Derek, this is so much hotter than I imagined.” Stiles was buzzing with pent-up nervous energy, hard and blushing. He dipped his index finger into the lube and slipped it in easily between the hard muscle of Derek’s arm and the soft tightness of his inner walls. Derek shivered, a bead of sweat dripping down his spine.

He looked at Stiles darkly. “Do you want to?”

“Yes! But...uh...you’re going to have to help me out. I’ve never done this before.”

Derek slowly pulled out and helped Stiles lube up until the jar was almost empty. They moved to the bed. Derek getting down on all fours in front of Stiles, spreading himself open. “Like this,” he said, showing Stiles to tuck his thumb into his palm like a duckbill. It reminded Stiles of making shadow puppets as a kid.

Stiles knew Derek could take so much more than just his bony little fist, but he still hesitated, placing his fingertips into Derek’s messy hole tentatively before slipping the rest of his hand inside.

Derek opened for him eagerly, moaning softly as Stiles eased in to the widest point in his fist, feeling Derek slick and hot and soft around him. He resisted the temptation to wiggle his fingers, instead just trying to get used to the feeling, before Derek grabbed him by the elbow and pulled him in wrist deep.

“Fuck,” Stiles gritted out, eyes wide, because Jesus Fucking Christ on a Pogo Stick Derek fit him like a goddamn glove. A hot wet slippery glove encasing his hand tight and snug and perfect. “Oh my God Derek this is fucking amazing. Is this...uh...is this okay for you? Because this is honestly the coolest thing I’ve ever felt.”

“Yeah,” Derek panted, “you can move.” When Stiles hesitated, Derek craned his head around over his shoulder. “Just in and out like you saw me do.”

So Stiles tried, tugging gently backwards before rocking back forwards, and he must have done it right because Derek let out another moan, arching his back and biting into one of Stiles’ pillows. Derek started to rock his hips backwards to meet Stiles’ thrusts, sinking the boy’s arm deeper and deeper into him.

How was fisting porn always so violent? This felt slow and tender to Stiles. Deep and intimate. After just a few minutes, they were both breathing hard and sweating, Derek’s moaning low in his throat as Stiles fucked into him. 

Stiles didn’t even think about it, just bent over and kissed Derek chastely at the base of his spine. Derek’s skin immediately prickled into a thousand goosebumps at the unexpected contact, his moan turning into a small gasp. Encouraged, Stiles continued to place small kisses on Derek’s back, coaxing out soft whines, feeling Derek’s ass tensing around him. Derek’s back was sweat-slippery soft skin over hard muscle. “So beautiful Derek,” he murmured against the skin, sneaking a taste of salt and smiling at the deep rumble of Derek’s resulting groan. He pulled back fast, lightly tugging on Derek’s rim with his fist. “I love the sounds you make,” he added, kissing Derek’s shoulder blade and thrusting back inside with a little twist to make sure his knuckles were hitting the prostate, making Derek keen.

Stiles rubbed his free hand up and down Derek’s back in comforting circles. “Love the way you arch your back. Love the way you need to be filled. Love how hungry you are for it.”

“Stiles…” Derek whispered. He craned his neck to face Stiles and there were tears in his eyes. Stiles just murmured comforting nonsense, working Derek’s ass at a steady pace, carding his fingers through Derek’s hair, scratching him behind the ears like a puppy. 

“Stiles...please?”

Stiles twisted his wrist and fucked in and out of Derek’s increasingly loose hole at a quickening pace. “Like that, Derek?” Stiles was suddenly aware of how tightly his jeans were constricting his hard-on. He unbuttoned his fly and pulled the jeans and his boxers down around his ass, freeing his cock, letting the leaking tip rub against the back of Derek’s thigh. Oh sweet friction! Stiles lazily let his dick rub up against Derek a couple more times before returning his focus to Derek’s ass. Stiles was trying to pace himself so his arm didn’t get too tired. The muscle was already starting to burn. Derek’s hole was loud with lube and movement, making obscene squelching noises as Stiles fistfucked him. It was the hottest sound Stiles had ever heard. “Fuck, listen to yourself! I know those werewolf ears can hear how fucking wet and sloppy you are.” 

Derek moaned in response, dick leaking precome onto Stiles’ sheets.

Stiles pulled out almost completely, with only his fingertips still inside. Derek gasped at the loss, whining and thrusting his hips backwards to try to get Stiles back inside him. Stiles laughed but indulged him, pushing his hand back in quickly and rocking against Derek’s prostate before pulling out again.

Derek’s satisfied grunt turned into a whine, which turned into a growl when Stiles pulled out completely. Hehehe. What was he expecting? Stiles prided himself on being a master troll. Truth be told, his arm was getting tired. No wonder tops in porn were always so buff. Stiles wasn’t _that_  weak (for a human), but he’d have to learn some exercises if he wanted to strengthen his fisting muscles. Stiles took off his t-shirt, brain quickly formulating something hot to say about Derek’s greedy hole when Derek reached behind himself and grabbed Stiles’ tired hand, thrusting it back inside himself, sliding his own hand in alongside it. And that was different. He was still surrounded by Derek, but the contrast of Derek’s muscular forearm and soft delicate asshole was heady. Derek fucked into himself faster than he had before, sliding against Stiles and grinding his teeth. Before Stiles could try to start up, Derek’s hand had found his and was guiding his movements. Stiles silently prayed that Derek wouldn’t pull his arm out of his socket and also silently marveled that _he and Derek Hale were holding hands inside of Derek’s ass_. _Derek was using Stiles’ arm as a dildo._ “Dude, are you using my arm as a dildo?” Okay, maybe not so silently. Derek didn’t say anything. His eyes were clenched tight in concentration as he used Stiles to punchfuck himself. They were pulling out completely before every thrust, and yeah, _that_ looked a lot more like the porn Stiles had seen. But Derek’s fingers clutched his so desperately. Stiles realized that this was probably the longest Derek had spent holding anyone’s hand in a very very long time. Thinking about it made his chest hurt, and more than anything he just wanted to feel closer to Derek. He pushed in deeper, breaking out of Derek’s grasp. Derek’s hand remained a frantic but reassuring presence by Stiles’ elbow. 

Stiles could feel Derek’s muscles moving around his arm and a second steady rhythm pulsing at his fingertips. Derek’s heartbeat. Stiles’ hand was shoved so far up Derek’s ass that he could feel his heartbeat, and it was without a doubt the most weirdly romantic, breathtakingly beautiful moment of his life. Stiles marveled, maybe stupidly, that he could literally feel Derek living around him-- it was fucking miraculous. And then there was nothing he could do. All of those pesky _feelings_ he’d been pushing aside came crashing down on him. All of that _liking_ and _caring_ and _concern_ and _affection_. Something in his chest that alternatingly ached and soared that wasn’t love but maybe could be the beginning of it. A desire to protect, as absurd as the idea of little human Stiles shielding beefcake werewolf Derek Hale sounded. A desire to provide safe haven from all the monsters and ghosts and bad memories. A desire to give when all life had done to Derek was take, to fill up some of the emptiness that Derek lived and breathed. Because the thing was that Derek _wasn’t_ just some brooding shell of a hot dude with washboard abs and an attitude problem. He was _real_ and _vital_ and _vulnerable_ and in a lot of ways just a normal guy with a gaping hole in his life where something normal or not supernatural or just not fucking tragic as shit was supposed to be. He needed someone to bring him down to earth and take care of him, even if it was just with goofy text messages and (really hot) sex. And Stiles could do that. He could absolutely fill that role for Derek.

“Fuck it,” Stiles said out loud, pulling out far enough that he could maneuver himself to Derek’s side and pull him into a kiss. It was awkward and uncomfortable and yeah maybe there was a reason Stiles never saw kissing in fisting porn, but the moment that Derek started to kiss him back would rank up there with scoring his first lacrosse goal and hitting Jackson with his Jeep as one of Stiles Stilinski’s All-Time Best Feelings Ever. He didn’t even think to get his tongue involved. He was too thrilled just pressing his mouth against Derek’s. By the time he pulled back, he felt ready to take on the fucking world. Tired arm be damned, he was ready to fistfuck Derek into next week and then cuddle the hell out of him afterwards. And then make pancakes. Before he could commence with his plan, Derek interrupted him.

“Um, why did you do that?”

Stiles had thought Derek had looked vulnerable the day Stiles had found the trunk, but it was nothing compared to the combination of abject terror and cautious hope in his eyes at that moment. “Because I like you, duh.”

“Really?”

Stiles wanted to track down every single person who had ever hurt Derek’s feelings and give them a piece of his mind. Or his bat. Maybe the bat would be better. “Yes, really! I like you. I _like_ like you. I want to go on dates with you and hold your hand at the movies and eat curly fries with you and make out in your car. Or my car. Or beds. Really anywhere. Well not _literally_ anywhere but--”

“Stiles.”

“Sorry. Yeah. You know what I mean.” There was a pause where they both just kind of looked at each other. Both of their hands were still in Derek’s ass. “So um. I like you. Do you like me? Check ‘yes’ for yes and ‘no’ for no?”

Derek cleared his throat. “Um yeah. Yeah I like you. This isn’t really a thing I do with anyone else. Or would do with anyone I didn’t like. But Stiles, you have to understand that our lives are--”

“Fuck that. Seriously. Fuck excuses. Fuck depriving yourself. Yeah our lives our complicated. Yeah our lives are full of constant bizarre peril. That’s not going to change. We might as well have some good things in there too, or else what’s even the point. Now, I don’t know if you noticed this, but our hands are still in your ass. I propose that I kiss you again, because I really like kissing you, and then fistfuck you into the mattress until you’re coming your brains out. Then I want to come. Possibly on you. Then I am going to cuddle you and kiss you some more. Tenderly and nicely. Then we are going to eat something. Maybe pancakes. _If_ you are a good boy who doesn’t complain about the aforementioned tender and nice cuddling. How does that sound?”

Derek looked like he was fighting off laughter, but his eyes were warm and affectionate. “Okay,” he nodded.

So Stiles leaned in again and kissed Derek, this time licking at the seam of his lips and biting him softly before pulling away. He was going to have to do a lot more of that. They intertwined their fingers and began to work in and out of Derek, twisting and grinding against his prostate with purpose. Derek used his free hand to grab his dick, jerking gently and mashing his face into Stiles’ pillow. Stiles grabbed his own neglected erection and started stroking, opening the floodgates that overwhelmed his brain-to-mouth filter. 

“I don’t care if it’s a werewolf power thing or not, you have the most amazing ass on the planet. I want to go through that trunk and item by item, do everything to your ass that I can. I want to fill you up and stretch you out and find your breaking point just so I can put you back together. Fuck, Derek!” 

Stiles was close, but Derek came first-- thick stripes onto Stiles’ sheets-- with a cry of “Stiles!” and Stiles managed to keep his mouth shut but God if he didn’t want to be the only name on Derek’s lips. He’d never been very possessive by nature, but he wanted every single one of Derek’s orgasms to belong to him.

They pulled out of Derek’s hole together, not untangling their hands, no matter how hot and sticky and tired they were. Derek flipped onto his back. (Right onto his own come, but whatever, they would do laundry later. Stiles’ sheets had seen worse.) His whole body was blushing, and he looked into Stiles’ eyes with something approaching reverence. Jesus fucking Christ Derek _did_ like him, and that realization-- solid and real-- did him in more than anything.

“I’m close,” Stiles groaned.

“I want you to come in me. Please.” There was a pause as Stiles tried to process what Derek had said. “I _will_ beg you, if you want.”

Yes. Stiles wanted. Stiles wanted very much. “Yeah, I like that idea. Beg for my come.” He tried to make it sound hot and confident without sounding like a cheesy porn dude. (He wasn’t sure if he was successful.)

It didn’t matter though, because somehow the execution was even hotter than the theory. Derek hooked his arms around his legs, pulling his knees to his chest and presenting his loose, red, thoroughly used hole. He looked at Stiles like Oliver Twist asking for another bowl of gruel. “Please come in me Stiles.” Derek’s anus was twitching, still not used to being empty.

Everything in Stiles made him want to surge forward and acquiesce, but that humming under his skin was back, that laser focus. So he just shrugged, stroking his dick leisurely and doing his best impression of someone who wasn’t impressed. “Eh.”

“Please come in me Stiles. Please mark me. Please give me your come. Please.” He sounded more desperate this time, his voice wavering slightly as he spoke.

Stiles looked down at Derek, spread open for him and waiting. “Where?” he asked, playing dumb, as if Derek’s body language wasn’t essentially a big Looney Toons arrow pointing to his ass.

Derek closed his eyes, his cheeks getting redder. “Stiles, please come in my ass. Shoot your load into my slutty used-up hole. Mark me on the inside. Mark me as yours.”

“Look at me.”

Derek opened his eyes. “Please Stiles…” He was the perfect image of submission. Not handcuffs and blindfolds submission, but wolf baring his throat submission. Perfect vulnerability. Perfect trust. It made him feel a wave of something warm and good in his chest. Like a heart orgasm.

The heat was pooling in Stiles’ belly, his balls tightening, and he barely had a chance to indulgently say “okay” and get the tip of his cock into Derek’s hole, when he was shooting into him. He stroked himself through his orgasm, resisting the urge to fuck into Derek’s slick loose heat, listening to Derek thanking him for his come, before collapsing onto the bed.

They were covered in sweat, and when Stiles cuddled up behind Derek, his hip landed right into lukewarm sticky jizz. Their fingers were still intertwined, hands and forearms greasy with residual lube.

“We are so gross right now,” Stiles hummed contentedly into the back of Derek’s neck, kissing him idly. “This is the best.” He felt warm and sleepy and stupid and very much in like if not a little bit in love.

“Stiles we should go clean up.”

Stiles wrapped his arms and legs around Derek like an octopus. “Nope. Not part of the plan. We are now entering into phase two: cuddling and kissing.” He tried and failed to manhandle Derek into turning to face him. “If you don’t cooperate, you will not get pancakes. In fact, you will get a bowl of gruel and have to watch _me_ eat pancakes. And I won’t share.”

“Hmph.”

“I can feel you smiling jackass, now turn around and kiss me, and if you do a good enough job I might even let you shower before pancakes.”

Derek rolled over, glaring at Stiles in the least convincing way possible. The corners of his mouth were twitching, and the sight of his face made Stiles feel warm and floaty. How could Stiles feel like he was flying when he was jelly-limbed and covered in bodily fluids? He’d Google it later. After all, it was time for phase two: sleepy post-sexytime cuddles. And kissing, he reminded himself. “Phase two means kissing. So pucker up sourwolf.”

Derek continued the world’s shittiest impression of being put-out. “You’re the worst.”

Sweaty, greasy, jizzy and grinning like idiots, Derek and Stiles kissed. Stiles pulled away after a moment to let Derek’s words really sink in. He took a deep breath and smiled. “Yeah,” he said, voice full of mirth and satisfaction, “I really am.”

**Notes for the Chapter:**

> this is by far the longest thing I've ever written. so I'm going to say thanks to some folks. 
> 
> thank you to everyone in the teen wolf fandom for being so supportive and awesome. thank you to everyone who commented, because seriously every single one of you made my flippin day when you did that. thanks for the kudos.
> 
> thanks specifically to [thing1](http://archiveofourown.org/users/thing1) for being like "hey have you checked out the teen wolf fanfic that's out there?" in the first place and sending me a huge email of fic recs and getting me here writing fic at all. and talking to me about this junk and supporting me. you are the best. to [neerdowellwolf](http://archiveofourown.org/users/neerdowellwolf) for feeding the flames of my teen wolf fic lust and perving on dylan o'brien and tyler hoechlin with me and listening to me waffle about what to do with this story. to [homosadpornien](http://archiveofourown.org/users/homosadpornien) for being the best writing buddy ever and reading all my late night DMs and writing amazing shit and sending me tragic sexts that make me want to cry.
> 
> friendship and community y'all. ;_;
> 
> also. *clears throat* last but not least I'm going to thank someone who will probably never read this, but if you do, hey honey, I bet some of that looked familiar. the derek to my stiles, as much as you would probably deny it. thanks for being cool about me staying up wild hours to write porn about teenage werewolves.


End file.
